Nitrone/Imine Selectivity Switch in Base-Catalysed Reaction of Aryl Acetic Acid Esters with Nitrosoarenes: Joint Experimental and Computational Study was written by Volpe, Chiara;Meninno, Sara;Roselli, Angelo;Mancinelli, Michele;Mazzanti, Andrea;Lattanzi, Alessandra. And the article was included in Advanced Synthesis & Catalysis in 2020.Computed Properties of C7H8O2S This article mentions the following:
Herein the authors report a mild and diastereoselective access to ketonitrones by reacting easily available aryl acetic acid esters and other active methylene compounds, with nitrosoarenes under catalytic loading of 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) at room temperature Depending on the substitution pattern and nature of the aryl moiety, a switch toward the formation of imines can be observed The mechanistic framework is put to scrutiny by exptl. and theor. studies, pointing to the formation of a nitroso aldol intermediate, whose fate toward one of the competing pathways, namely hydride transfer or elimination, would depend upon the NOH/CHα relative acidities. In the experiment, the researchers used many compounds, for example, Methyl 2-thienylacetate (cas: 19432-68-9Computed Properties of C7H8O2S).
Methyl 2-thienylacetate (cas: 19432-68-9) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Computed Properties of C7H8O2S
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics